Best Chicago Itinerary 4 days – Things To Do This Weekend

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Read about Chicago Itinerary 4 days with the best things to do in Chicago city tour.

Chicago Itinerary 4 days
View from Willis Tower

Chicago – the third biggest city in the United States of America (USA), is one of the world’s great cities to visit, with so many beautiful attractions. The splendid skyline on freshwater Lake Michigan will enchant you with its vibrant & lively city life, cultural happenings, architectural wonders, charming neighborhoods, delicious food, and fascinating history.

This city is perfect for all ages and interests as it has many varied things to do. This city is often named as “The Windy City” and is famous for many festivals like Music and Taste of Chicago food festival. Due to its historic location on Big Route 66 of US, Chicago is also the famous historic city that is worth visiting too. So let’s take a virtual tour of the best things to do in Chicago city tour – Chicago Travel Guide.

Best Things to do in Chicago City Tour – Chicago Travel Guide
Chicago Skyline view

Note: I was hosted by ChooseChicago(official destination marketing organization) and its co-partners – CityPass Chicago, Big Bus Chicago, Chicago Architecture Foundation Center, Chicago Food Planet and Shakespeare Theater to feel Chicago, but views and opinions are my own, not influenced by anyone.

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Chicago Itinerary 4 Days – Best Things to do in Chicago City Tour 


A 110-story skyscraper was the tallest building once upon a time and has held its title for about 25 years.  Currently, this is the 2nd tallest tower in the USA and the 16th tallest in the world. Designed by famous architect Adrian Smith who is known for designing the famous tallest buildings like Burj Khalifa(Dubai) too. 

Best Things to do in Chicago City Tour – Chicago Travel Guide
View from the top

Step onto its 103rd floor, an Observatory Deck, also known as The SkyDeck Chicago, for the splendid views of the city. There are unique 4ft extended transparent glass balconies on this floor where you can feel hanging in the air above the ground from the 103rd floor and observe the city under your feet.

Chicago Itinerary 4 days - Willis Tower Ledge
Put your foot forward on Willis Tower Ledge


  • General Admission – 25 USD – Adults
  • 17 USD – Children (Ages 3 to 11)
  • There are also fast pass where you can skip the queue.
  • Chicago CityPASS holders get General Admission + Ledge + Bonus 2nd-time entry during Night/Evening view within the same day.

Opens 365 days a year

TIP: Go early morning so that you avoid huge crowds and queues. Select a clear day so that you can see far places.


A public park within the Loop area is the most famous among Chicagoans. This park is situated in the heart of downtown and always hosts many events, farmer markets on special days, greenery, and art / sculptural displays; it is like the town square of Chicago. This spectacular gathering point is surrounded by a beautiful skyline, like an oasis within the concrete cityscape. In winter, during snowy times, this park converts into a beautiful ice rink for skating around.

Visit Millennium Park is highly recommended in your Chicago itinerary 4 days tour.

TICKETS – Free to Enter


Best Things to do in Chicago City Tour – Chicago Travel Guide

A wonderful mirror-finished steel sculpture that looks like a drop of mercury is located in Millennium Park and is officially known as “The Cloud Gate.” Designed by Indian-born British artist Mr. Anish Kapoor this steel sculpture with special mirror polish reflects the city skyline in various manners. Due to its curvature and fine polish, you can see many distorted and multiple versions of the city skyline in this sculpture.

This sculpture was the result of one of the design competitions and now is the most photogenic location or the symbol of this city. Adults and children especially enjoy this place to see their distorted faces and also the city skylines, which is the same as mirror house effects.

TICKETS – Free to Enter


Best Things to do in Chicago City Tour – Chicago Travel Guide
Water fountain from the lips of multimedia animated face

Two massive 50-foot glass towers face each other with an excellent display of art, video sculpture combination of residents of Chicago. With the display of faces of residents, also the water fountains gushing out from the lips at regular intervals of time, this fountain is a favorite among kids and even adults too in the summertime or hot afternoons. A large amount of water is thrown from the lips of the multimedia display from both sides, and it looks like a person is throwing water from their mouth.

TICKETS – Free to Enjoy


Best Things to do in Chicago City Tour – Chicago Travel Guide
View from top of 360 Chicago

From 1000 feet above the ground, on the 94th floor, enjoy the splendid views of Lake Michigan and stunning city views with an adorable skyline from the top. At present this is the 4th tallest building in Chicago and 9th tallest in the USA. This residential building houses many hotels & offices too, and it is the 3rd highest residential tower in the world.

Step on to its Observatory deck – 360 Chicago for having 360 ° views of the whole city with a clear picture of the distance to 80 miles on a clear day.

Best Things to do in Chicago City Tour – Chicago Travel Guide
View of city


  • General Admission – 25 USD – Adults
  • 15 USD – Children (Ages 3 to 11)
  • Chicago CityPASS holders get Express Entry Admission.

It is open 365 days a year.


Here you can also feel the most unique and thrilling experience of the world by feeling like you are falling down from the 94th floor.  Tilt is the transparent whole façade windows where you have to hold the railings and stand to look down, and within a few seconds, this façade is tilted down to a certain angle and left in that position for a few minutes. During this tilt on the edge of the floor and leaning against the window, you will feel like falling down from the top floor.  This kind of experience cannot be found anywhere in the tallest building in the world.

For the TILT experience, you must purchase separate tickets for 8 USD. Chicago Citypass holders get some discount for Tilt tickets.


Admire the magnificent and world-famous Chicago skyline, which is also one of the world’s tallest skylines. This city skyline boasts of having four of America’s tallest buildings.

Where to get the best view of Chicago’s Skyline? – Chicago Itinerary 4 Days

  • Solidarity Drive – Stretching from Grant Park to Adler Planetarium. This stretch has a lovely waterfront with small grass stretches and benches. Chicago skyline view from Solidarity drive
  • From the grounds of Adler Planetarium
    Best Things to do in Chicago City Tour – Chicago Travel Guide
    Chicago Skyline view


  • Near the North End of Navy Pier

    Best Things to do in Chicago City Tour – Chicago Travel Guide
    Dramatic clouds over the Navy Pier with skyline view

  • At the top of observatory deck of John Hancock Center. Best Things to do in Chicago City Tour – Chicago Travel Guide
  • From the Grant Park Chicago skyline view from Grant Park


Best Things to do in Chicago City Tour – Chicago Travel Guide

A 75 minutes boat cruise to see the famous architecture across the Chicago River. With live commentary about these buildings and architects, you will sail across 40 iconic buildings and will get the opportunity to learn about Chicago’s history, how this city is built and rebuilt after the Great Fire, and also upcoming architectural growth in this city. 

You must be amazed to know the world-famous architects of many famous tallest buildings and who belong to Chicago. This cruise covers all three branches – Old Post Office Building, Willis Tower & East Bank Club. 

Architecture River Cruise in Chicago


Best Things to do in Chicago City Tour – Chicago Travel Guide

Located on Lake Michigan, this aquarium houses many exotic species of marine creatures, including sea horses, stingray fish, dolphins, whales, etc., from local  Lake Michigan, the world-famous Amazon rainforest, wide oceans, and Caribbean Reefs. It has approximately 32,000 aquatic creatures. 

Best Things to do in Chicago City Tour – Chicago Travel Guide
Inside Shedd Aquarium

Activities at Shedd Aquarium –

  • Touch the textured sea creatures in Polar Play Zone
  • Grab a 4D show featuring many interesting sensational marine life short movies
  • Enjoy the Dolphin show.


  • General Admission – 39.95 USD – Adults
  • 29.95 USD – Children (Ages 3 to 11)
  • 4 D Upgrade – 4.95 USD
  • Chicago CityPASS holders get all Shedd Exhibits, shows and 4D experience.

Outside the Shedd Aquarium, there is a café / Restaurant for eating out with fantastic Chicago skyline views.

Best Things to do in Chicago City Tour – Chicago Travel Guide
View of Chicago skyline from the restaurant of Aquarium


Best Things to do in Chicago City Tour – Chicago Travel Guide

The Field Museum, which is a natural history museum, is one of the largest natural history museums in the world.  It has been opened in 1893 and has approximately 24 million exhibits from all over the world. It showcases rich cultural and historical exhibits from ancient civilizations like Egypt, Asia, Africa, and the ancient Americas. 

The central atrium of Stanley Field Hall welcomes you with a 37m Titanosaur, which is the key feature of this museum. For the last year 125 years, this museum has added precious exhibits every year. You can also grab a 3D show to feel how the displays are excavated or the story behind the exhibits.

Best Things to do in Chicago City Tour – Chicago Travel Guide
Inside the Museum
  • All-Access Pass (Includes all General Admission to exhibitions, ticketed exhibitions & one 3D movie)                                                                                          40 USD – Adults                                                                                                                 29USD –  Children (Ages 3 to 11)
  • Basic Admission (Only Includes all General Admission to exhibitions)              26 USD – Adults                                                                                                                19 USD – Children (Ages 3 to 11)
  • Chicago CityPass holders get the All-Access Pass


Best Things to do in Chicago City Tour – Chicago Travel Guide
Inside the Planetarium

This was the first planetarium in the USA, which included an actual observatory. Located in Museum Campus, Grant Park, beside Lake Shore you get a chance to experience the Solar System, the history of telescopy, landing on the moon, and many varieties of shows.


  • UNLIMITED (All Exhibitions, unlimited shows + Atwood sphere)                            50 USD – Adults                                                                                                                39USD – Children (Ages 3 to 11)
  • MUSEUM ENTRY + 2 (All Exhibitions + 2 shows + Atwood sphere)                       35 USD – Adults                                                                                                         24USD  Children (Ages 3 to 11)
  • ONLY MUSEUM ENTRY                                                                                                  19 USD – Adults                                                                                                               08 USD – Children (Ages 3 to 11)
  • Chicago CityPass holders get the MUSEUM ENTRY + 2 access.


Best Things to do in Chicago City Tour – Chicago Travel Guide

Located on the south of Magnificent Mile at Michigan Avenue, a white-colored iconic building of this city. It is one of the most famous buildings in Chicago. This clock tower is designed in per Gothic style and with intricate details on the limestone façade, which is a perfect classy example of architecture.


Best Things to do in Chicago City Tour – Chicago Travel Guide
Dramatic clouds over the Navy Pier with skyline view

Your visit to Chicago is incomplete without visiting Navy Pier. Located on the shoreline of Lake Michigan, it is spread across 50 acres with many parks, waterfront restaurants, amusement rides, drama theaters, IMAX movie theater, and event areas, and is one of the top family attractions in the Mid-West of the USA. 

It is also famous for its 65-meter Centennial Wheel and other amusement rides. In summer, you can also experience fireworks over the city skyline, which occurs twice a week. There are many cruise options from here, like dinner cruises.

Best Things to do in Chicago City Tour – Chicago Travel Guide

An antique style of the trolley which is a free shuttle from State street and few stops in between takes you to Navy Pier.


Best Things to do in Chicago City Tour – Chicago Travel Guide
Inside the Theater

Located on Navy Pier this non-profit theater broadcast Shakespearean productions.  This award-winning theater is the city’s most versatile performing Arts Center of the city.

Best Things to do in Chicago City Tour – Chicago Travel Guide
Wizard of Oz ending
Best Things to do in Chicago City Tour – Chicago Travel Guide
Outside the theater on Navy Pier


Chicago Children'sMuseum

Located at Navy Pier, this museum is famous among young children (ages 10 and under). This 3 story museum has a big splash and many DIY theme-based activities.


Best Things to do in Chicago City Tour – Chicago Travel Guide

This Gothic-styled tower which was built in 1869, is very iconic as it is one in a couple of buildings that survived the Great Chicago Fire on October 8 – 10, 1871. These 3 days of fire burnt the whole city, but as this tower is made up of limestone, unlike other nearby wooden buildings, it has survived. It looks like a small castle, the second oldest water tower on the great Magnificent Mile.


Best Things to do in Chicago City Tour – Chicago Travel Guide

This iconic historic area in Chicago which consists of world-class architectural buildings, parks, theaters, restaurants and vibrant shopping street forms the true downtown of Chicago. At the south end of Loop is the museum area.

MUST DO ACTIVITIES IN CHICAGO | Best Things to do in Chicago City Tour – Chicago Travel Guide

  • Stroll across the Magnificent Mile to feel the vibrant and eclectic vibes of this fascinating city. Magnificent Mile is also known as Le Boul Mich and it starts from Oak Street to the riverfront at Michigan Avenue. This upscale stretch is famous for high-end shopping and will amaze you with many choices.  It houses largest Ralph Lauren store in the world and also many fine dining avenues. Hancock Tower and other famous sky scrappers are also located across this stretch. Best Things to do in Chicago City Tour – Chicago Travel Guide
  • Take an Architecture Tour depending on your choice of transportation. Architecture tours are given by walking tours, river tours, L(public transportation) tours to admire the history of Chicago’s architecture.
  • Chicago is foodies heaven and there are many authentic Chicago style signature dishes which you must try on when visiting this place. Pamper your taste buds by authentic Chicago style deep dish pizzas, signature styled hot dogs and gourmet popcorn. These signature dishes cannot be found anywhere in the world. Go for Chicago Food Tour.
  • Ride the L which is an elevated railway track passing through the busy streets of Chicago. These tracks are surrounded by skyline and it is one of the best ways to feel the city vibes. This L runs throughout the city and comes under the public transportation system. Best Things to do in Chicago City Tour – Chicago Travel Guide
  • Grab a seat at Chicago Shakespeare Theatre or at Chicago Teater Chase. I was invited for the wonderful Wizard of Oz show by Chicago Shakespeare Theater and it was really wonderful. Best Things to do in Chicago City Tour – Chicago Travel Guide
  • Admire the murals or street art on Magnificent Mile or State street.  Best Things to do in Chicago City Tour – Chicago Travel GuideBest Things to do in Chicago City Tour – Chicago Travel Guide
  • Walk along the river or cross the bridges with beautiful views of the river.

    Best Things to do in Chicago City Tour – Chicago Travel Guide
    Walk over the bridges on river

How To Reach Chicago? | Best Things to do in Chicago City Tour – Chicago Travel Guide

By Air – Chicago’s International airport – O’Hare is one of the busiest airports in the world. All major national & international airlines connect Chicago.

Check Air Tickets to Chicago (Book your flight to Chicago)

By RailAmtrak train network connects this city with around 50 trains arriving and departing daily.

By Car – This city is connected through wide Interstates & highways like I-90, I-94, I-55, I-210, and I-294.

By Bus – You can also reach here by buses from Greybound lines, Peoria Charter from nearby counties and Mega bus lines.

How To Commute In Chicago? | Best Things to do in Chicago City Tour – Chicago Travel Guide

By foot, Taxis / Uber, Public transportation from CTA/ RTA. The public transport comprises of 8 rail lines across the city which are L, 200 buses and 11 Metra lines from suburbs.

You can also purchase 1 day, 3 Day or 7 Day CTA pass for unlimited bus and L rides. Many people hire bikes to move around the city. Click here to check your routes and pass details on CTA’s official website.

You can also take Hop On Hop Off Big Bus tours which showcase all best attractions in their whole day trip. Also they organize night tours too.  Big Bus tours are very convenient and I found it very interesting as they have live commentary by friendly guides who use to tell some interesting facts and history of the city. 

Best Things to do in Chicago City Tour – Chicago Travel Guide

Avoid self-drive as parking can be a hassle. If you are bringing your car, then find the nearby affordable parking slots through Spot On App.

What To Eat & Drink In Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide

  • Deep Dish Chicago styled Pizza especially at Lou Malnati’s and Giordano’s Pizza. Your visit to this city is incomplete if you don’t taste these special deep crust or stuffed crust pizzas from Lou Malnati’s or Giordano’s.
  • Gourmet flavored Popcorn. 
  • This city is also famous for craft breweries and so lot many options to have craft beer.
  • Tap water is safe for drinking.
  • As this city is foodie heaven you will find cuisines from all over the world. There are more than 7300 restaurants and in which 22 of them are Michellein Starred ones.

Where To Stay in Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide

Where to stay in Chicago is a very important thing as this city has many beautiful locations with many hotel choices. During my Chicago city tour, I stayed at 2 locations to feel the different feel of the city. My choices are

Where to stay in Chicago
Where to stay in Chicago?

EMBASSY SUITES BY HILTON DOWNTOWNClick here to book your stay at Embassy Suites. 

Where to stay in Chicago?
Huge and grand Hotel Lobby

Positives of Embassy Suites

  • Lavish Breakfast Buffet
  • Lavish complimentary evening Happy Hours spread
  • Big room size
  • Close proximity to many restaurants as it is located on the famous restaurant street of Chicago

WYNDHAM GRAND CHICAGO RIVERFRONTClick here to book your stay at Wyndham Grand.

Positives of Wyndham Grand Chicago Riverfront

  • View of the river from the room
  • Located in a prime location with many famous attractions at a walkable distance.

When is the best time to visit Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide

  • The best time to visit Chicago is from late Springs (late April) through Fall (mid-October).
  • May, June and July are peak seasons with many tourists and outdoor events. Summer is the peak season
  • In April, August, September, and October the crowd is manageable and you will find hotels in good rates too.
  • Afterward, the weather is extreme cold by falling down to -6 degrees Celsius. This extreme cold slowly starts from November and then gear up from December to March-end. If you love snow, festive markets of Christmas then December is the ideal month to visit. You will find many Germany styled festive Christmas markets and can go for ice skating too.

Best Things to do in Chicago City Tour – Chicago Travel Guide

Where To Shop in Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide

  • Take a look at shopping street of Magnificent Mile, Macy’s at State Street, Burlington’s at downtown, Bloomingdale’s.
  • Daily and essential needs can be bought from Walgreens and 7-Eleven grocery stores.
  • If you are driving or renting a car then go for the premium factory outlet malls for high-end brand shops at affordable range. For this you have to drive to the suburb of Aurora which houses Chicago Premium Outlet Mall and you will find all big brands here like Coach, Michael Kors, Tommy Hilfiger, Calvin Klein, Nautica, Timberland, Columbia, Nike, Adidas, Crocs and many more.


  • If you are visiting both the Observatory decks, museums, aquarium, and planetarium then purchase CityPass as it costs 108USD for Adults and 89USD for Children. Then this pass will be a money savior option with time-saving too at many places due to skipping of queues.
  • Book your stay near the Downtown, Magnificent Mile or State Street.
  • This is a windy city, so be prepared for it by carrying a light jacket with you.
  • As many places can be done by walking tours, and the gardens are also widespread, you have to walk a lot and therefore wear comfortable footwear.
  • Chicago is safe with normal precautions to take. Their touristy locations are very safe but some suburbs of south Chicago which are residential are not safe.
  • People of this city are welcoming and soft-spoken. Families traveling with children will find this city very enjoyable.
  • Try the famous local food.
  • Take a river or lake cruise.
  • If you are renting a car then select pickup of a rented car from Airport as it is a very cost-effective option.
  • Chicago Tourism is classified or categorized into
    • Architectures tours,
    • Museum Tours,
    • Nature – Parks / Gardens tours,
    • Lake / River Tours, Food & Culture Tours, and
    • Sports / Dance Music Festival tours.

You can select as per your choice and as per my recommendation do at least one activity from each category. 

Best Things to do in Chicago City Tour – Chicago Travel Guide
Walking across the Loop


  • Chi Bar
  • Redhead Piano Bar
  • House of Blues
  • Kingston Mines
  • Bub City
  • The Bassment


Chicago is an event and festival city. And so you can find many events or festivals all year round. Check out more events and shows on by clicking here.

  • World-famous Taste of Chicago
  • Chicago Blues Festival
  • Chicago Jazz Festival
  • Wells Street Art Festival
  • Glencoe Festival of Art
  • Chicago International Film Festival
  • Lollapalooza
  • Chicago Gourmet


  • This city consists of 77 neighborhoods.
  • What do you mean by Chicago? – Pottawatawine Native Americans used to live here before any explorers came to this part. They used to call this land “Shikaakwa,” which means a smelly onion. They named it smelly onion as this land was a big swamp before and was very smelly. After the arrival of French explorers, traders & missionaries in the late 17th century, this land further developed into a city named after “Shikaakwa” to “Chicago.”
  • This city has the only unique river which flows backward in the world. Chicago River is flown back by the reversal technique to divert the sewage away.
  • The First Blood Bank of the USA was founded here, and the first open-heart surgery in the world took place here.
  • The Great Chicago Fire of 1871, which ran across 3 days and whose initial spark is still unknown, devastated the whole city as the buildings were made of wood. But after the 19th century, this city was rebuilt with new building materials and techniques, which can also survive such disasters. And within 20 years, this city created a beautiful skyline that matches world-class standards.
  • It is the home to world-famous architects who have designed many of the world’s tallest buildings.
  • Many Hollywood films have been shot here. Also, a Bollywood film – Dhoom 3, starring Aamir Khan and Abhishek Bachchan, has been shot here.

Chicago itinerary 4 days - best things to do in Chicago

Chicago Itinerary 4 Days

  • DAY 1 – Late evening arrival – Took a stroll across the restaurant street and, due to some jetlag, went to sleep early.
  • DAY 2 – Started Chicago city tour by Chicago Big Bus tours (started early)
  • Lunch stop
  • Willis Tower Observatory Deck
  • Millennium Park
  • From late Afternoon till Evening, I took River Architecture Cruise
  • Had Dinner
  • DAY 3 – Early morning start – Headed to 360 Chicago Observatory Deck
  • Then proceeded to Shedd Aquarium
  • Field Museum
  • Alder Planetarium
  • After having lunch at Shedd Aquarium with a view, I returned back to Chicago Architecture Center for Exhibits tour displaying models of many famous buildings of the world and Chicago city designs.
  • DAY 4 –  Riverwalk in the morning
  • Strolling across Magnificent Mile
  • Take a Chicago food tour, a 3 hours food tour with the history of Chicago.
  • Evening at Downtown Loop and again shopping at Magnificent Mile. All done by walking tours.
  • DAY 5 – Morning at Navy Pier.
  •                Lunch at Navy Pier
  •                Attended Play – “The Wizard of Oz” at Chicago Shakespeare Theater
  •  Shopping at Downtown
  • Dinner at the famous Giordano’s Pizzeria (At Giordano’s there is always a waiting of 30 to 40 minutes and it is always full of people). There are many Giordano’s Pizza outlets in the city.
  • DAY 6 – Early morning, headed to car renting outlet at International Airport and then proceeded to Aurora for Chicago Premium Outlet Mall and then to explore Illinois state and its counties like Urbana, Champaign, Peoria, and the capital city – Springfield.
Chicago itinerary 4 days - best things to do in Chicago
A complete Chicago Trip Guide

Now you how perfect a Chicago itinerary 4 days and do let me know how this city excites you? I would love to know your candid views in the comments below. Also, use hashtag #ChicagoHome with your lovely photos in this beautiful city on your social media network. 


Are you in Illinois, then visit beautiful county Champaign which is 130 to 140 miles away from Chicago. 

If you are on USA trip then read these guides for

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  1. Thanks so much for the awesome guide! I live only a 6 hour drive from here in Minnesota, and am hoping to visit soon! Your post only motivated me to fill out my gas tank and make a trip even at this time of night 🙂

  2. Chicago is one of my favorite cities in the U.S. However, it has been almost 10 years since I last visited. I have seen many of these attractions but I would definitely do them all again. I haven’t seen the Crown Fountain or the Tilt Museum, so maybe they didn’t exist when I was there or I just didn’t know about them. Field Museum is my absolute favorite!

  3. This is an excellent guide for Chicago. Lots of details about attractions and places to stay. I absolutely love this city and visited it many times. I especially like to go shopping on the Magnificent Mile and walk on the lake promenade.

  4. I’ve been to Chicago many times, but sadly not for Taste of Chicago. Time to rectify this! And I never knew that the river was the only one in the world that flows backward.

  5. Chicago looks so cool! The bean is definitely on my list of first place to visit here. I also love museums so Field museum it is! It’s crazy that it has 24 million exhibits from all over the world. I’ve never tried Hop On Hop Off Bus but I think I would love to do it as well.

    1. Thanks Ha for reading through and yes this natural history museum is interesting and you would truly love riding on Hop on Hop off bus as it passes through wonderful buildings all around.

  6. I loved this post, Yukti. It is such a comprehensive post on all the best things to do in Chicago. I could never make it to the Windy City when I was in the US. And all I wanted to see was the Bean. But there are so many other interesting things to do here. I am loving the panoramic views and the multimedia water fountain. My son is quite excited too. Hope we get to go there soon.

  7. What an interesting read. I had no idea Chicago had so much to offer. I particularly like that falling down from the top floor experience. Itll be great to test ojt my fear of my heights 🙂

    1. Yes Kristina, feeling like falling from heights is very scary and I saw many people stepped back as soon as the window tilted. Though we know we are leaning on window but then also it gives real fall experience.

  8. I’ve heard lots of great things about Chicago but I’ve never quite made it there. It woulds like a very interesting city with lots of things to do, although I think I’d give the tilt experience a miss! I love the buildings along the water – looks like they are really making the most of the setting.

    1. You would love Chicago and yes buildings beside the water really looks beautiful and that is why it looks like modern Venice

  9. I would so love to visit Chicago, it’s one of just a few major cities I haven’t been to yet. Not sure I could do that Tilt Experience though, looks terrifying. Would love to see the skyline from the top of the John Hancock Tower though.

    1. Yes the skyline from top is amazing thing to view here. Also the city looks very big and spread out from top of John Hancock Tower.

  10. I didn’t realize Chicago is the third largest city in the US. The view from Willis Tower and John Hancock Tower is incredible. The Crown Fountain is so much fun and I would really enjoy a cruise on the Chicago River and see the architecture.

  11. This is such a comprehensive guide to Chicago, Yukti! I’ve been told many times I would like visiting Chicago and your post confirms it. There are many attractions you’ve described here that are reminiscent of my home city (Boston MA). For instance, the Water Tower, reminds me of a much lighter version of Trinity Church. One day soon, I will visit “The Windy City” for myself. And I will look to your post for guidance.

    1. Wow good to know that this city is having many similarities with your city Boston, MA. Thanks for finding my post useful and it is great that it convinces you to visit this Windy City. I too got surprised by its beauty and vibrancy when I visited this city.

  12. I went to Chicago in 2009 and I remember loving it! Great city and a great guide. You hit all the big points and provided some really useful and interesting information – I didn’t know there was a Bollywood film filmed in Chicago – how interesting!

    How did you like the glass floor at the Willis Tower? That looks exciting and scary. Same with the TILT experience – I have yet to do something like that, but it looks so fun.

    1. Yes Lena, It was scary for few minutes initially to walk on that glass floor and even that Tilt but afterwards you feel Okay. And famous Bollywood film “Dhoom 3” starring top most Bollywood actors if filmed here and there special chasing sequences. It is great you loved the information given in this article.

  13. Love, love this post! Such a wealth of information. We visited Chicago many years ago for just 24 hours and did the architectural river tour. It was incredible! The second highlight was the American Girls store (travelling with a five year old at the time!) I’d love to return with the kids and visit the Adler Planetarium and the natural history museum. Those look to be state of the art places we’d all love. And of course we’d have to visit Navy Pier!

  14. A very detailed and well put together guide, that will surely help a lot of visitors, especially first timers. It is so humbling to see a such a big and towering city, once from such heights and once from the streets. Thank you so much for sharing 🙂

  15. Willis Tower Ledge, the Tilt, the Bean… so many cool things to see, they certainly love their heights in Chicago… And I would go and find some street art… And at the end of the day, a meal in a hip restaurant, so many to choose from I’m sure…

  16. Omg, that tilt experience looks so crazy! I am so afraid of heights, but I strangely want to try this. I have been to Chicago a couple of times, but feel like I have missed out on so much after reading your post. I’d like to also check out the crown fountain next time I visit 🙂

    1. Yes Tilt is crazy and in other way adventurous experience too. I hope on your next visit, you visit some more exciting attractions.

  17. Gosh! Never thought that there are a lot of things to see and do in Chicago. We’re visiting next month to attend a cousin’s wedding and would love to maximize the trip.

    We’re definitely looking forward to experience the Chicago Skyline and a visit to the aquarium and planetarium.

    Thank you so much for sharing these tips. They are really helpful for first timers like us.

    1. Good to know you are visiting next month and you would definitely love this beautiful city. Thanks for finding this post useful.

  18. I have been to Chicago years ago, and loved it. But there are so many things I haven’t seen or done. The bean is such an iconic part of the city. I like the idea of the Tilt Experience, but not sure I would do it. A backward flowing river? That’s so interesting. I would love to visit Chicago again. Great post.

    1. Yes I too admired the idea of backward flowing river which is just created to avoid the garbage being dumped from other side. Amazing concept to keep the water clean.

  19. A fantastic guide to read, especially for me as Chicago is one of the cities I want to hit up next in the USA. I always wanted to see the Bean and the Fountain but I would also love to run along the river (which I think is the one they turn green for Saint Paddy’s day) and along the lake shores. I love cities which blends in with green parks, lakes and sea. Can’t wait to get out there one day.

  20. Yes! As someone who was born and raised in Chicago, I support all of this! And I love how you named Lou Malnatti’s — everyone always says Giordano’s but if you’re from Chicago… man that’s the best pizza.

    1. Thanks for loving this post and I loved both lou Malnati’s and Giordano’s pizza. Both are unique in its own ways. I must say all should try them when they visit Chicago.

  21. Chicago is such a beautiful city, but highly underrated in the USA. The first time I went there I was so shock by how pretty and unique the city was and how little people know this about it. You really covered everything there is to do in the city perfectly!

    1. I second you Sam, that I had also not heard many things about Chicago and for me also it was underrated before going, but I was surprised to see the beauty of this city. Thanks for finding this post very comprehensive.

  22. Chicago would be exactly one city we would visit if we were flying to the US. I just imagine it exciting and lively. I like the variety that you present in your article. I think so I could imagine a program in the city too. Thank you for the great info.

  23. I lived in Chicago from 2010 until 2017, the city is beautiful and is really looked after. During the tourist season, you really need to be mindful of pick pockets.

    The planetarium does a really cool even in the summer for adults called Adler After Dark. Millennium Park does a lot of free events in the summer evenings which are perfect for date nights or things to do with friends.

    Honestly, I miss Chicago so much and I can’t wait to move back one day.

    1. Wow, it is great you lived in such a great city. I too loved many parts of that city and being there for only a week, I too miss it a lot.

  24. I absolutely LOVE Chicago and I’ve been a few times. I love the Willis Tower (formerly Sears, but didn’t know it was designed by the same architect as the Burj Khalifa that I haven’t seen!) and I love standing on the glass floors looking straight down. Two things I didn’t know about (and wonder if they are new since I lasted visit almost 4 years ago) are the Crown Fountain (so cool) and the Tilt Experience. That is right up this adventurer’s alley!

    1. Heather, it is great you too love Chicago. I too loved it. Also I guess that Crown fountain and Tilt are newly added attraction. It is great to see Chicago is adding up many attractions every year.

  25. I have I always wanted to see Chicago but never get around to it! It looks so beautiful and so clean there! My dream is to go there and have photoshoots around the city especially the gorgeous buildings in the background and of course by the Bean! Love all your pics and so gorgeous! ❤️

  26. I love Chicago, it’s one of my favorite cities in the U.S. You have some great recommendations here, especially the architecture tour! One thing on your list I have never done is the tilt experience, it looks scary but really fun.

  27. I think Chicago is the most beautiful city in the States (obviously from my opinion) and I think everyone who want to visit the USA should visit Chicago. This was a really comprehensive guide for Chicago and I think any first time traveler should visit it.

  28. I am surprised to see that some buildings are designed in Gothic style, but they still look very modern. The city’s lake side is amazing, it looks like the seaside! I think this is a nice for a family to spend a week holiday as well.

  29. I used to live in Chicago and you really found all the best places! I have yet to see the Bean so I think it’s time I go back for a visit. I just really love all the waterfront places. I’m not sure I’m ready for either the Sky Deck or the Tilt though!

  30. wow there are so many insane things to see here! I would love to visit the The SkyDeck Chicago especially! It is great that it is open all year round. Thank you for the tip to get there early to avoid the crowds!

  31. I’m yet to cross the Altantic Ocean! I hope to visit USA in near future. Ofcourse Chicago is in my wishlist – seeing the bean early in the morning before the crowds pour in, is something I’m hoping to do. Obviously Skydeck & Tilt experience is the next thing I want to do.
    Architecture river cruise sounds interesting. Shedd Aquarium and Natural History museum would be undoubtedly my daughter’s favourite places.
    The historic water tower is amusing. Its not even as old as it looks! Esp., with the towering modern sky scrapers around it, it feels all the more old! Very very fascinating!

    1. I hope you would love this vibrant city and your daughter would enjoy many things here as this is a family city and all young children love aquarium, museum,3D shows and activities on Navy Pier. Thanks Bhushavali for reading and loving this article.

  32. Chicago is not too far from me and my husband and I love visiting. So much to do! The pizza, the buildings, and the feel of the city is just so amazing to us!

    1. Wow Carolyn it is great that you live nearby to this beautiful city. I too loved the pizza, buildings and the vibes of this city.

  33. This is indeed a complete tour de force of Chicago city. Lovely guide that brings to the fore the remarkable attractions of Chicago which is definitely a unique destination in the US, in its own right. The photos of the views from the SkyDeck Chicago, had me literally on the brink of vertigo! Looks really fascinating. Would love to watch a performance at the Shakespeare Theatre, the Wizard of Oz brought back memories of childhood.

    1. Thanks Sandy for your lovely words but really I would say that skyDeck Chicago makes you go through all that Vertigo moments. I too loved that cute performance of Wizard of Oz and yes that childhood memories are really beautiful.

  34. What a fun trip! It looks like you hit all the highlights. This is a good reminder that I need to go visit friends in Chicago soon! I think I’ll suggest the Aquarium when I’m there.

  35. I’ve been wanting to visit Chicago for YEARS – and this is only feeding that desire, that’s for sure. Between the tilt experience, the aquarium, the Bean, and soooo many other experiences, I know it would be the most amazing trip!

  36. Great guide to Chicago! I’ve always wanted to return for a few days! I’ve only left the airport for a couple of long layovers, but I would really love to spend more time there. Willis Tower looks like a lot of fun with the glass floor!

    1. Yes Leah, you would truly enjoy this city. I too loved that glass floor at Willis Tower but they allowed only 9 seconds on it, due to heavy crowd waiting for it.

  37. I’ve been wanting to get to Chicago for the past few years now, but the only time I’ve had available has been during the winter. I’m definitely not going to shoot myself in the foot with my first experience. I’m not sure I’d be brave enough to do the tilt experience…I might cry. But getting a picture with The Bean is definitely up there. I’ve saved this post because your itinerary is perfect for me! I can’t wait to visit!

    1. Thanks Rachelle and even I am like you. I too could not go for TILT and sent my hubby and children there. But for Ledge I was OK though did not look down a lot.

  38. I have yet to go to Chicago only seen in movies and films and of course blogs like yours. Its really impressive the amount of skyscrapers there. Really interesting is the sculpture “The Cloud Gate” at the Millenium Park. I like how it reflects the skyline. Also of interest to me is the way Lake Michigan looks – more like the sea : So cool! I will for sure come back to reference your itinerary when my day to visit Chicago comes!

    1. Thanks Adele, and even for me this lake looks like sea and even you can see small tides or waves in it. I cannot see the other end from the top of building. You would truly enjoy Chicago.

  39. The city’s skyscrapers are truly impressive. Chicago is one of the good place I wish to visit after watching many American rom-com movies through the eyes. How is it during winter or December season?!

  40. Chicago is one of the few major cities in the US I haven’t been to yet so this gave me a lot of inspiration. There are lots of incredible skyscrapers that I’d like to see and I had no idea you can take an architecture river cruise. That seems like a great way to see it all in a relaxing way! I’d also love to go to the observation deck in the Wallis Tower as I love heights and the views seem incredible.

  41. Chicago is like a second home city to me as I visit frequently. That said, I’m familiar with all the places you listed in the post! I particularly love Millennium Park and Navy Pier, and never miss an opportunity to visit. Reading this makes me want to return soon. A very detailed guide.

  42. Chicago is such an ideal city. There are so many things to do! The last time I’ve been to Chicago in 2001, I didn’t get to do a lot of things because it was such a short visit. But you definitely had a lovely experience. Your travel itinerary is so detailed. I need to refer to this post when I visit Chicago in the future, this time with my husband and kids.

    1. Yes it is a very beautiful city and especially with kids. Now your boys will love it and go again this time for long time.

  43. This third largest city of USA is so impressive. So much to see and do. Guess will not be able to cover all of this in one day. Loved your pictures, especially the one you clicked outside the theater on Navy pier

    1. Thanks Anahita, this city has many things to do and for me 5 days were not enough to see the whole city. Chicago has many wonderful things to do.

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